The French explorer Jean Baptiste Bénard de La Harpe first mapped the site of Haileyville in 1719 during his expedition to the Arkansas River.

In 1898 D. M. Hailey, M.D., established the town of Haileyville, when he claimed a tract of land east of McAlester and opened the area's first coal mines.

A Confederate veteran, Hailey had first moved into Indian Territory in 1868 to practice medicine and before long had become involved in several business ventures.

Haileyville, in the Choctaw Nation, was a company town, which was a common feature of coal-mining communities.

Haileyville remained the division point of the Rock Island Railroad until 1958, when the offices moved to El Reno.

The community and its close neighbor, Hartshorne, are known as the "twin cities" of Pittsburg County due to their proximity.

At the time of its founding, Haileyville was located in Gaines County, a part of the Moshulatubbee District of the Choctaw Nation.

[6] According to the United States Census Bureau, the city has a total area of 1.0 square mile (2.6 km2), all land.